Some songs not playing on iPod in iPhone

I've had about 4 iPhones over the past few years and before that i had a second generation iPod nano. Over this period of time, I purchased a lot of music thru iTunes either on my computer or thru the one in iPhone. I then transferred music over from each iPhone to the new one. Usually this has worked fine, however since I upgrade to 4S, I've noticed that songs I have purchased thru iTunes on past iPhones (or the old iPod) no longer play. Although when just testing out different ones now I notice some old ones will play and others won't. I'm not sure if it's just a random issue or not. If I have it on shuffle and it comes to one of those songs, it either stops, or oddly enough, it will start playing a different song but still show the other song's album cover and information. If I play a song individually and it doesn't work, it will either just do nothing or it will skip to the next song immediately. I can't quite figure out what's happening with this but I'm guessing it has to be a migration issue.
Has anyone else experienced this and know how I can fix it? Is it just a matter of authorizing something within iTunes or iPhone?
Please let me know. Thanks!
-Pooja

This is actually happenening on my non-itunes bought songs...basically songs that got converted from another source...perhaps from my old MP3 player from Sony...the problem is, they used to work on my ipod, and now they don't. I did try resetting the ipod, but that didn't seem to help.

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